Dimethylformamide → Anthraquinone

HRID 1973706Notes

Reaction equation

HRID 1973706 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]2[C:11](=[O:12])[CH:10]=[CH:9][C:7](=[O:8])[C:5]=2[CH:6]=1.C(O[CH:17]=[CH:18][CH:19]=[CH2:20])(=O)C.CN(C)C=O>C(O)(=O)C>[CH:17]1[C:10]2[C:11](=[O:12])[C:4]3[C:5](=[CH:6][CH:1]=[CH:2][CH:3]=3)[C:7](=[O:8])[C:9]=2[CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 85301,4-NaphthoquinoneHCID 151951,3-Butadienyl acetate

Product 1

HCID 6780AnthraquinoneYield 90%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
125 °C

Procedure

15.8 parts by weight of naphthoquinone and 13.0 parts by weight of 1-acetoxybutadiene in 40 parts by volume of dimethylformamide and 10 parts by volume of acetic acid are stirred for 6 hours under nitrogen at 45° - 50° C. Air is then passed in and the batch is stirred for 2 hours at 125° C. After cooling, the anthraquinone which has precipitated is filtered off and washed with dimethylformamide. 18.0 g (90% of theory) of anthraquinone of melting point 284° C are obtained.

Workup

  1. temperatureAfter cooling
  2. customthe anthraquinone which has precipitated
  3. filtrationis filtered off
  4. washwashed with dimethylformamide

Sources & evidence

ORD record
ord-67bad0e098a54b7688f8a8265d727a07
Source dataset
uspto-grants-1976_12
Patent number
US03998857

Reaction notes

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